Whether you're dressing up a short-sleeve t-shirt and jeans or swapping battered men's Timberland PRO™ work boots for a casual after-work style, we've got all the looks you need. Dark brown chukka boots add a sophisticated touch to a long-sleeve and vest combo. Chelsea boots perfectly straddle the line between casual and dressy, and lace-up boots are always there when you need to lean business casual for a work party.

Our dress shoes for men, including men’s oxfords, brogues, boots, and other men’s casual dress shoes, are designed for comfort that transitions seamlessly from the office to happy hour. Plus, our casual men’s leather dress shoes are perfect for going out on the weekends. Pick a pair of boots with a plain toe look for long days out and add some athletic outerwear.

Need something more solid than loafers or suede sneaker boots? Many of our men's dress shoe styles can match even our hiking boots & shoes for outdoor durability. With water-resistant and waterproof construction, you can shoulder your commuter backpack even in the rain. Unparalleled craftsmanship and rugged outsoles mean you can take your dress ankle boots anywhere from the streets of New York to a low-key hike. Match your leather boots with men's belts to add style and stability to your outfit.

Our men's dress boots and shoes are made for walking. You expect comfort from your hikers and steel toes: why not expect it from your dress shoes? Look for shoe styles with our breathable Ortholite® insoles or anti-fatigue technology to keep you going. You'll get the comfort of memory foam with the keep-going durability you need for daily wear. Wide-toe chukka boots to best seller Oxfords that beat out any wingtip boot style, you can find the perfect pair of boots to add a special touch to your look.